Organometallic compound, organic light-emitting device including the same, and diagnostic composition including the organometallic compound

ABSTRACT

An organometallic compound represented by Formula 1:wherein, in Formula 1, R1 to R12 and R16 are the same as described in the specification.

CROSS-REFERENCE TO RELATED APPLICATION

This is a continuation application of U.S. application Ser. No.16/372,836, filed on Apr. 2, 2019, which claims priority to KoreanPatent Application Nos. 10-2018-0038354, filed on Apr. 2, 2018, and10-2019-0036865, filed on Mar. 29, 2019, in the Korean IntellectualProperty Office, and all the benefits accruing therefrom under 35 U.S.C.§ 119, the contents of which are incorporated herein in their entiretyby reference.

BACKGROUND 1. Field

One or more embodiments relate to an organometallic compound, an organiclight-emitting device including the organometallic compound, and adiagnostic composition including the organometallic compound.

2. Description of the Related Art

Organic light-emitting devices (OLEDs) are self-emission devices whichhave superior characteristics in terms of a viewing angle, a responsetime, brightness, a driving voltage, and a response speed, and whichproduce full-color images.

In an example, an organic light-emitting device includes an anode, acathode, and an organic layer disposed between the anode and thecathode, wherein the organic layer includes an emission layer. A holetransport region may be disposed between the anode and the emissionlayer, and an electron transport region may be disposed between theemission layer and the cathode. Holes provided from the anode may movetoward the emission layer through the hole transport region, andelectrons provided from the cathode may move toward the emission layerthrough the electron transport region. The holes and the electronsrecombine in the emission layer to produce excitons. These excitonstransit from an excited state to a ground state, thereby generatinglight.

Meanwhile, luminescent compounds may be used to monitor, sense, ordetect a variety of biological materials including cells and proteins.An example of these luminescent compounds is a phosphorescentluminescent compound.

Various types of organic light emitting devices are known. However,there still remains a need in OLEDs having low driving voltage, highefficiency, high brightness, and long lifespan.

SUMMARY

One or more embodiments relate to a novel organometallic compound and anorganic light-emitting device including the same.

Additional aspects will be set forth in part in the description whichfollows and, in part, will be apparent from the description, or may belearned by practice of the presented embodiments.

An aspect of the present disclosure provides an organometallic compoundrepresented by Formula 1:

wherein, in Formula 1, R₁ to R₁₂ and R₁₆ may each independently beselected from hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a substituted or unsubstituted C₁-C₆₀ alkylgroup, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅),—Ge(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), —P(═O)(Q₈)(Q₉), and —P(Q₈)(Q₉), at leastone selected from R₁ to R₆ may each independently be a group representedby Formula 2:

-   -   wherein, the number of carbon atoms included in Formula 2 may be        4 or more,    -   R₁₃ in Formula 2 may be hydrogen, deuterium, a C₁-C₂₀ alkyl        group, a deuterium-containing C₁-C₂₀ alkyl group, a C₃-C₁₀        cycloalkyl group, or a deuterium-containing C₃-C₁₀ cycloalkyl        group,    -   R₁₄ and R₁₅ in Formula 2 may each independently be a C₁-C₂₀        alkyl group, a deuterium-containing C₁-C₂₀ alkyl group, a C₃-C₁₀        cycloalkyl group, or a deuterium-containing C₃-C₁₀ cycloalkyl        group,    -   indicates a binding site to a neighboring atom,    -   at least two selected from R₁ to R₉ and R₁₆ in Formula 1 may        optionally be linked to form a C₅-C₃₀ carbocyclic group        unsubstituted or substituted with at least one R_(1a) or a        C₂-C₃₀ heterocyclic group unsubstituted or substituted with at        least one R_(1a),    -   R_(1a) may be the same as defined in connection with R₇,    -   at least one substituent of the substituted C₁-C₆₀ alkyl group,        the substituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀        alkynyl group, the substituted C₁-C₆₀ alkoxy group, the        substituted C₃-C₁₀ cycloalkyl group, the substituted C₁-C₁₀        heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenyl        group, the substituted C₁-C₁₀ heterocycloalkenyl group, the        substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxy        group, the substituted C₆-C₆₀ arylthio group, the substituted        C₁-C₆₀ heteroaryl group, the substituted monovalent non-aromatic        condensed polycyclic group, and the substituted monovalent        non-aromatic condensed heteropolycyclic group may be selected        from:    -   deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H,        —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino        group, an amidino group, a hydrazine group, a hydrazone group, a        carboxylic acid group or a salt thereof, a sulfonic acid group        or a salt thereof, a phosphoric acid group or a salt thereof, a        C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl        group, and a C₁-C₆₀ alkoxy group;    -   a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl        group, and a C₁-C₆₀ alkoxy group, each substituted with at least        one selected from deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H,        —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a        nitro group, an amino group, an amidino group, a hydrazine        group, a hydrazone group, a carboxylic acid group or a salt        thereof, a sulfonic acid group or a salt thereof, a phosphoric        acid group or a salt thereof, a C₃-C₁₀ cycloalkyl group, a        C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a        C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀        aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl        group, a monovalent non-aromatic condensed polycyclic group, a        monovalent non-aromatic condensed heteropolycyclic group,        —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), —Ge(Q₁₃)(Q₁₄)(Q₁₅),        —B(Q₁₆)(Q₁₇), —P(═O)(Q₁₈)(Q₁₉), and —P(Q₁₈)(Q₁₉);    -   a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a        C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a        C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio        group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromatic        condensed polycyclic group, and a monovalent non-aromatic        condensed heteropolycyclic group;    -   a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a        C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a        C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio        group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromatic        condensed polycyclic group, and a monovalent non-aromatic        condensed heteropolycyclic group, each substituted with at least        one selected from deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H,        —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a        nitro group, an amino group, an amidino group, a hydrazine        group, a hydrazone group, a carboxylic acid group or a salt        thereof, a sulfonic acid group or a salt thereof, a phosphoric        acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀        alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a        C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a        C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a        C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio        group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromatic        condensed polycyclic group, a monovalent non-aromatic condensed        heteropolycyclic group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅),        —Ge(Q₂₃)(Q₂₄)(Q₂₅), —B(Q₂₆)(Q₂₇), —P(═O)(Q₂₈)(Q₂₉), and        —P(Q₂₈)(Q₂₉); and    -   —N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), —Ge(Q₃₃)(Q₃₄)(Q₃₅),        —B(Q₃₆)(Q₃₇), —P(═O)(Q₃₈)(Q₃₉), and —P(Q₃₈)(Q₃₉), and    -   Q₁ to Q₉, Q₁₁ to Q₁₉, Q₂₁ to Q₂₉, and Q₃₁ to Q₃₉ may each        independently be selected from hydrogen, deuterium, —F, —Cl,        —Br, —I, a hydroxyl group, a cyano group, a nitro group, an        amino group, an amidino group, a hydrazine group, a hydrazone        group, a carboxylic acid group or a salt thereof, a sulfonic        acid group or a salt thereof, a phosphoric acid group or a salt        thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀        alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group,        a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a        C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀        aryl group substituted with at least one selected from a C₁-C₆₀        alkyl group, and a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a        C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalent        non-aromatic condensed polycyclic group, and a monovalent        non-aromatic condensed heteropolycyclic group.

Another aspect of the present disclosure provides an organiclight-emitting device including: a first electrode, a second electrode,and an organic layer disposed between the first electrode and the secondelectrode, wherein the organic layer includes an emission layer and atleast one organometallic compound described above.

The organometallic compound in the emission layer may act as a dopant.

BRIEF DESCRIPTION OF THE DRAWING

These and/or other aspects will become apparent and more readilyappreciated from the following description of the embodiments, taken inconjunction with the FIGURE which is a schematic view of an organiclight-emitting device according to an embodiment.

DETAILED DESCRIPTION

The present disclosure will now be described more fully with referenceto exemplary embodiments. The disclosure may, however, be embodied inmany different forms and should not be construed as being limited to theembodiments set forth herein, rather, these embodiments are provided sothat this disclosure will be thorough and complete, and will fullyconvey the concept of the disclosure to those skilled in the art.Advantages, features, and how to achieve them of the present inventiveconcept will become apparent by reference to the embodiment that will bedescribed later in detail, together with the accompanying drawings. Thisinventive concept may, however, be embodied in many different forms andshould not be limited to the exemplary embodiments.

Reference will now be made in detail to embodiments, examples of whichare illustrated in the accompanying drawings, wherein like referencenumerals refer to like elements throughout. In this regard, the presentembodiments may have different forms and should not be construed asbeing limited to the descriptions set forth herein. Accordingly, theembodiments are merely described below, by referring to the FIGURES, toexplain aspects of the present description. As used herein, the term“and/or” includes any and all combinations of one or more of theassociated listed items. Expressions such as “at least one of,” whenpreceding a list of elements, modify the entire list of elements and donot modify the individual elements of the list.

It will be understood that when an element is referred to as being “on”another element, it can be directly in contact with the other element orintervening elements may be present therebetween. In contrast, when anelement is referred to as being “directly on” another element, there areno intervening elements present.

It will be understood that, although the terms first, second, third etc.may be used herein to describe various elements, components, regions,layers, and/or sections, these elements, components, regions, layers,and/or sections should not be limited by these terms. These terms areonly used to distinguish one element, component, region, layer, orsection from another element, component, region, layer, or section.Thus, a first element, component, region, layer, or section discussedbelow could be termed a second element, component, region, layer, orsection without departing from the teachings of the present embodiments.

The terminology used herein is for the purpose of describing particularembodiments only and is not intended to be limiting. As used herein, thesingular forms “a,” “an,” and “the” are intended to include the pluralforms as well, unless the context clearly indicates otherwise.

The term “or” means “and/or.” It will be further understood that theterms “comprises” and/or “comprising,” or “includes” and/or “including”when used in this specification, specify the presence of statedfeatures, regions, integers, steps, operations, elements, and/orcomponents, but do not preclude the presence or addition of one or moreother features, regions, integers, steps, operations, elements,components, and/or groups thereof.

Unless otherwise defined, all terms (including technical and scientificterms) used herein have the same meaning as commonly understood by oneof ordinary skill in the art to which this general inventive conceptbelongs. It will be further understood that terms, such as those definedin commonly used dictionaries, should be interpreted as having a meaningthat is consistent with their meaning in the context of the relevant artand the present disclosure, and will not be interpreted in an idealizedor overly formal sense unless expressly so defined herein.

Exemplary embodiments are described herein with reference to crosssection illustrations that are schematic illustrations of idealizedembodiments. As such, variations from the shapes of the illustrations asa result, for example, of manufacturing techniques and/or tolerances,are to be expected. Thus, embodiments described herein should not beconstrued as limited to the particular shapes of regions as illustratedherein but are to include deviations in shapes that result, for example,from manufacturing. For example, a region illustrated or described asflat may, typically, have rough and/or nonlinear features. Moreover,sharp angles that are illustrated may be rounded. Thus, the regionsillustrated in the figures are schematic in nature and their shapes arenot intended to illustrate the precise shape of a region and are notintended to limit the scope of the present claims.

“About” or “approximately” as used herein is inclusive of the statedvalue and means within an acceptable range of deviation for theparticular value as determined by one of ordinary skill in the art,considering the measurement in question and the error associated withmeasurement of the particular quantity (i.e., the limitations of themeasurement system). For example, “about” can mean within one or morestandard deviations, or within ±30%, 20%, 10%, 5% of the stated value.

An aspect of the present disclosure provides an organometallic compoundrepresented by Formula 1 below:

In Formula 1, R₁ to R₁₂ and R₁₆ may each independently be selected fromhydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —Ge(Q₃)(Q₄)(Q₅),—B(Q₆)(Q₇), —P(═O)(Q₈)(Q₉), and —P(Q₈)(Q₉), and Q₁ to Q₉ are the same asdescribed above.

For example, R₁ to R₁₂ and R₁₆ may each independently be selected from:

-   -   hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano        group, a nitro group, an amino group, an amidino group, a        hydrazine group, a hydrazone group, a carboxylic acid group or a        salt thereof, a sulfonic acid group or a salt thereof, a        phosphoric acid group or a salt thereof, —SF₅, C₁-C₂₀ alkyl        group, and a C₁-C₂₀ alkoxy group;    -   a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted        with at least one selected from deuterium, —F, —Cl, —Br, —I,        —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a        cyano group, a nitro group, an amino group, an amidino group, a        hydrazine group, a hydrazone group, a carboxylic acid group or a        salt thereof, a sulfonic acid group or a salt thereof, a        phosphoric acid group or a salt thereof, a C₁-C₁₀ alkyl group, a        cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a        cycloctyl group, an adamantanyl group, a norbornanyl group, a        norbornenyl group, a cyclopentenyl group, a cyclohexenyl group,        a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a        bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a        bicyclo[2.2.2]octyl group, a phenyl group, a biphenyl group, a        terphenyl group, a naphthyl group, a pyridinyl group, and a        pyrimidinyl group;    -   a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a        cycloctyl group, an adamantanyl group, a norbornanyl group, a        norbornenyl group, a cyclopentenyl group, a cyclohexenyl group,        a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a        bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a        bicyclo[2.2.2]octyl group, a phenyl group, a biphenyl group, a        terphenyl group, a naphthyl group, a fluorenyl group, a        phenanthrenyl group, an anthracenyl group, a fluoranthenyl        group, a triphenylenyl group, a pyrenyl group, a chrysenyl        group, a pyrrolyl group, a thiophenyl group, a furanyl group, an        imidazolyl group, a pyrazolyl group, a thiazolyl group, an        isothiazolyl group, an oxazolyl group, an isoxazolyl group, a        pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a        pyridazinyl group, an isoindolyl group, an indolyl group, an        indazolyl group, a purinyl group, a quinolinyl group, an        isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl        group, a quinazolinyl group, a cinnolinyl group, a carbazolyl        group, a phenanthrolinyl group, a benzimidazolyl group, a        benzofuranyl group, a benzothiophenyl group, an        isobenzothiazolyl group, a benzoxazolyl group, an        isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an        oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a        dibenzothiophenyl group, a benzocarbazolyl group, a        dibenzocarbazolyl group, an imidazopyridinyl group, and an        imidazopyrimidinyl group;    -   a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a        cycloctyl group, an adamantanyl group, a norbornanyl group, a        norbornenyl group, a cyclopentenyl group, a cyclohexenyl group,        a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a        bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a        bicyclo[2.2.2]octyl group, a phenyl group, a biphenyl group, a        terphenyl group, a naphthyl group, a fluorenyl group, a        phenanthrenyl group, an anthracenyl group, a fluoranthenyl        group, a triphenylenyl group, a pyrenyl group, a chrysenyl        group, a pyrrolyl group, a thiophenyl group, a furanyl group, an        imidazolyl group, a pyrazolyl group, a thiazolyl group, an        isothiazolyl group, an oxazolyl group, an isoxazolyl group, a        pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a        pyridazinyl group, an isoindolyl group, an indolyl group, an        indazolyl group, a purinyl group, a quinolinyl group, an        isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl        group, a quinazolinyl group, a cinnolinyl group, a carbazolyl        group, a phenanthrolinyl group, a benzimidazolyl group, a        benzofuranyl group, a benzothiophenyl group, an        isobenzothiazolyl group, a benzoxazolyl group, an        isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an        oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a        dibenzothiophenyl group, a benzocarbazolyl group, a        dibenzocarbazolyl group, an imidazopyridinyl group, and an        imidazopyrimidinyl group, each substituted with at least one        selected from deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂,        —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro        group, an amino group, an amidino group, a hydrazine group, a        hydrazone group, a carboxylic acid group or a salt thereof, a        sulfonic acid group or a salt thereof, a phosphoric acid group        or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group,        a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a        cycloctyl group, an adamantanyl group, a norbornanyl group, a        norbornenyl group, a cyclopentenyl group, a cyclohexenyl group,        a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a        bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a        bicyclo[2.2.2]octyl group, a phenyl group, a biphenyl group, a        terphenyl group, a naphthyl group, a fluorenyl group, a        phenanthrenyl group, an anthracenyl group, a fluoranthenyl        group, a triphenylenyl group, a pyrenyl group, a chrysenyl        group, a pyrrolyl group, a thiophenyl group, a furanyl group, an        imidazolyl group, a pyrazolyl group, a thiazolyl group, an        isothiazolyl group, an oxazolyl group, an isoxazolyl group, a        pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a        pyridazinyl group, an isoindolyl group, an indolyl group, an        indazolyl group, a purinyl group, a quinolinyl group, an        isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl        group, a quinazolinyl group, a cinnolinyl group, a carbazolyl        group, a phenanthrolinyl group, a benzimidazolyl group, a        benzofuranyl group, a benzothiophenyl group, an        isobenzothiazolyl group, a benzoxazolyl group, an        isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an        oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a        dibenzothiophenyl group, a benzocarbazolyl group, a        dibenzocarbazolyl group, an imidazopyridinyl group, an        imidazopyrimidinyl group, and —Si(Q₃₃)(Q₃₄)(Q₃₅); and    -   —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —Ge(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇),        —P(═O)(Q₈)(Q₉), and —P(Q₈)(Q₉), and    -   Q₁ to Q₉ and Q₃₃ to Q₃₅ may each independently be selected from:    -   —CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃, —CH₂CD₂H, —CH₂CDH₂,        —CHDCH₃, —CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃, —CD₂CD₂H, and        —CD₂CDH₂;    -   an n-propyl group, an iso-propyl group, an n-butyl group, an        iso-butyl group, a sec-butyl group, a tert-butyl group, an        n-pentyl group, an iso-pentyl group, a sec-pentyl group, a        tert-pentyl group, a phenyl group, and a naphthyl group; and    -   an n-propyl group, an iso-propyl group, an n-butyl group, an        iso-butyl group, a sec-butyl group, a tert-butyl group, an        n-pentyl group, an iso-pentyl group, a sec-pentyl group, a        tert-pentyl group, a phenyl group, and a naphthyl group, each        substituted with at least one selected from deuterium, a C₁-C₁₀        alkyl group, and a phenyl group.

In an embodiment, R₁ to R₉ and R₁₆ may each independently be hydrogen,deuterium, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkyl group, or—Si(Q₃)(Q₄)(Q₅). Q₃ to Q₅ are the same as described in this disclosure.

In one or more embodiments, R₁ to R₁₂ and R₁₆ may each independently beselected from:

-   -   hydrogen, deuterium, a methyl group, an ethyl group, an n-propyl        group, an iso-propyl group, an n-butyl group, a sec-butyl group,        an iso-butyl group, a tert-butyl group, an n-pentyl group, a        tert-pentyl group, a neo-pentyl group, an iso-pentyl group, a        sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an        n-hexyl group, an iso-hexyl group, a sec-hexyl group, a        tert-hexyl group, an n-heptyl group, an iso-heptyl group, a        sec-heptyl group, a tert-heptyl group, an n-octyl group, an        iso-octyl group, a sec-octyl group, a tert-octyl group, an        n-nonyl group, an iso-nonyl group, a sec-nonyl group, a        tert-nonyl group, an n-decyl group, an iso-decyl group, a        sec-decyl group, a tert-decyl group, a methoxy group, an ethoxy        group, a propoxy group, a butoxy group, a pentoxy group, a        cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a        cycloctyl group, an adamantanyl group, a norbornanyl group, a        norbornenyl group, a cyclopentenyl group, a cyclohexenyl group,        a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a        bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a        bicyclo[2.2.2]octyl group, a phenyl group, a biphenyl group, a        terphenyl group, a naphthyl group, a pyridinyl group, a        pyrimidinyl group, a carbazolyl group, a fluorenyl group, a        dibenzosilolyl group, a dibenzofuranyl group, a        dibenzothiophenyl group, and —Si(Q₃)(Q₄)(Q₅);    -   a methyl group, an ethyl group, an n-propyl group, an iso-propyl        group, an n-butyl group, a sec-butyl group, an iso-butyl group,        a tert-butyl group, an n-pentyl group, a tert-pentyl group, a        neo-pentyl group, an iso-pentyl group, a sec-pentyl group, a        3-pentyl group, a sec-isopentyl group, an n-hexyl group, an        iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an        n-heptyl group, an iso-heptyl group, a sec-heptyl group, a        tert-heptyl group, an n-octyl group, an iso-octyl group, a        sec-octyl group, a tert-octyl group, an n-nonyl group, an        iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an        n-decyl group, an iso-decyl group, a sec-decyl group, and a        tert-decyl group, each substituted with at least one deuterium;        and    -   a methoxy group, an ethoxy group, a propoxy group, a butoxy        group, a pentoxy group, a cyclopentyl group, a cyclohexyl group,        a cycloheptyl group, a cycloctyl group, an adamantanyl group, a        norbornanyl group, a norbornenyl group, a cyclopentenyl group, a        cyclohexenyl group, a cycloheptenyl group, a        bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a        bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a        phenyl group, a biphenyl group, a terphenyl group, a naphthyl        group, a pyridinyl group, a pyrimidinyl group, a carbazolyl        group, a fluorenyl group, a dibenzosilolyl group, a        dibenzofuranyl group, and a dibenzothiophenyl group, each        substituted with at least one selected from deuterium and a        C₁-C₁₀ alkyl group, and    -   Q₃ to Q₅ are the same as described above.

In one or more embodiments, R₁ to R₁₂ and R₁₆ may each independently beselected from:

-   -   hydrogen, deuterium, —F, a cyano group, a nitro group, —SF₅,        —CH₃, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, groups represented        by Formulae 9-1 to 9-66, groups represented by Formulae 9-1 to        9-66 in which at least one hydrogen is substituted with        deuterium, groups represented by Formulae 10-1 to 10-249, groups        represented by Formulae 10-1 to 10-249 in which at least one        hydrogen is substituted with deuterium, or —Si(Q₃)(Q₄)(Q₅)        (wherein Q₃ to Q₅ are the same as described above), but        embodiments of the present disclosure are not limited thereto:

In Formulae 9-1 to 9-66 and 10-1 to 10-249, * indicates a binding siteto a neighboring atom, Ph indicates a phenyl group, and TMS indicates atrimethylsilyl group.

The “groups represented by Formulae 9-1 to 9-66 in which at least onehydrogen is substituted with deuterium” may refer to, for example,groups represented by Formulae 9-501 to 9-552: The “groups representedby Formulae 9-1 to 9-66 in which at least one hydrogen is substitutedwith deuterium” may refer to, for example, groups represented byFormulae 9-501 to 9-552:

The “groups represented by Formulae 10-1 to 10-249 in which at least onehydrogen is substituted deuterium” may refer to, for example, groupsrepresented by Formulae 10-501 to 10-510:

At least one selected from R₁ to R₆ may each independently be selectedfrom a group represented by Formula 2:

The number of carbon atoms included in Formula 2 may be 4 or more (forexample, 4 to 20, 4 to 15 or 4 to 10),

-   -   R₁₃ in Formula 2 may be hydrogen, deuterium, a C₁-C₂₀ alkyl        group, deuterium-containing C₁-C₂₀ alkyl group, a C₃-C₁₀        cycloalkyl group, or a deuterium-containing C₃-C₁₀ cycloalkyl        group,    -   R₁₄ and R₁₅ in Formula 2 may each independently be a C₁-C₂₀        alkyl group, deuterium-containing C₁-C₂₀ alkyl group, a C₃-C₁₀        cycloalkyl group, or a deuterium-containing C₃-C₁₀ cycloalkyl        group, and    -   * indicates a binding site to a neighboring atom.

The terms “a deuterium-containing C₁-C₂₀ alkyl group” and “adeuterium-containing C₃-C₁₀ cycloalkyl group” as used herein each referto a C₁-C₂₀ alkyl group substituted with at least one deuterium and aC₃-C₁₀ cycloalkyl group substituted with at least one deuterium,respectively. For example, the term “a deuterium-containing methylgroup” as used herein refers to —CDH₂, —CD₂H, and —CD₃.

The term “C₁-C₂₀ alkyl group” as used herein refers to, for example, amethyl group, an ethyl group, an n-propyl group, an iso-propyl group, ann-butyl group, a sec-butyl group, an iso-butyl group, a tert-butylgroup, an n-pentyl group, a tert-pentyl group, a neo-pentyl group, aniso-pentyl group, a sec-pentyl group, a 3-pentyl group, a sec-iso-pentylgroup, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, atert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptylgroup, a tert-heptyl group, an n-octyl group, an iso-octyl group, asec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonylgroup, a sec-nonyl group, a tert-nonyl group, an n-decyl group, aniso-decyl group, a sec-decyl group, or a tert-decyl group, butembodiments of the present disclosure are not limited thereto.

The term “C₃-C₁₀ cycloalkyl group” as used herein refers to, forexample, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acycloctyl group, an adamantanyl group, a norbornanyl group, abicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, abicyclo[2.2.1]heptyl group, or a bicyclo[2.2.2]octyl group, butembodiments of the present disclosure are not limited thereto.

In an embodiment, at least one selected from R₂ to R₅ in Formula 1 maybe a group represented by Formula 2.

In one or more embodiments, one selected from R₂ to R₅ in Formula 1 maybe a group represented by Formula 2, and R₁ to R₆ other than the grouprepresented by Formula 2 R₁ to R₆ may be hydrogen.

In one or more embodiments, in Formula 1,

-   -   1) R₂ may be a group represented by Formula 2 and R₁ and R₃ to        R₆ may be hydrogen,    -   2) R₃ may be a group represented by Formula 2 and R₁, R₂ and R₄        to R₆ may be hydrogen,    -   3) R₄ may be a group represented by Formula 2 and R₁ to R₃, R₅        and R₆ may be hydrogen,    -   4) R₅ may be a group represented by Formula 2 and R₁ to R₄ and        R₆ may be hydrogen,    -   5) R₅ may be a group represented by Formula 2, R₃ may be a        substituted or unsubstituted C₁-C₆₀ alkyl group, or a        substituted or unsubstituted C₃-C₁₀ cycloalkyl group, and R₁,        R₂, R₄ and R₆ may be hydrogen,    -   6) R₄ may be a group represented by Formula 2, R₂ may be a        substituted or unsubstituted C₁-C₆₀ alkyl group, or a        substituted or unsubstituted C₃-C₁₀ cycloalkyl group, and R₁,        R₃, R₅ and R₆ may be hydrogen,    -   7) R₂ may be a group represented by Formula 2, R₅ may be a        substituted or unsubstituted C₁-C₆₀ alkyl group, or a        substituted or unsubstituted C₃-C₁₀ cycloalkyl group, and R₁,        R₃, R₄ and R₆ may be hydrogen,    -   8) R₄ may be a group represented by Formula 2, R₅ may be a        substituted or unsubstituted C₁-C₆₀ alkyl group, or a        substituted or unsubstituted C₃-C₁₀ cycloalkyl group, and R₁,        R₂, R₃ and R₆ may be hydrogen, or    -   9) R₄ may be a group represented by Formula 2, R₃ may be a        substituted or unsubstituted C₁-C₆₀ alkyl group, or a        substituted or unsubstituted C₃-C₁₀ cycloalkyl group, and R₁,        R₂, R₅ and R₆ may be hydrogen,

In one or more embodiments, R₇ and R₉ in Formula 1 may not be hydrogen.

In one or more embodiments, R₇ and R₉ in Formula 1 may not be hydrogen,and R₈ and R₁₆ may be hydrogen.

In one or more embodiments, R₁₆ in Formula 1 may be hydrogen.

In one or more embodiments, R₇ and R₉ in Formula 1 may not be hydrogen,and R₇ and R₉ may be identical to each other.

In one or more embodiments, R₇ and R₉ in Formula 1 may not be hydrogen,and R₇ and R₉ may be different from each other.

In one or more embodiments, R₇ and R₉ in Formula 1 may not be hydrogen,R₇ and R₉ may be different from each other, and the number of carbonatoms included in R₇ may be greater than that of carbon atoms includedin R₉.

In one or more embodiments, R₇ and R₉ in Formula 1 may eachindependently be a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkyl group, or a substitutedor unsubstituted C₆-C₆₀ aryl group.

In one or more embodiments, at least one of R₇ and R₉ in Formula 1 mayeach independently be a substituted or unsubstituted C₂-C₆₀ alkyl group,a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, or a substitutedor unsubstituted C₆-C₆₀ aryl group.

In one or more embodiments, R₁₃ in Formula 2 may be hydrogen ordeuterium.

In one or more embodiments, R₁₃ in Formula 2 may be a C₁-C₂₀ alkylgroup, a deuterium-containing C₁-C₂₀ alkyl group, a C₃-C₁₀ cycloalkylgroup, or a deuterium-containing C₃-C₁₀ cycloalkyl group.

In one or more embodiments, R₁₄ and R₁₅ in Formula 2 may be differentfrom each other.

In one or more embodiments, in Formula 2,

-   -   R₁₃ may be hydrogen, deuterium, —CH₃, —CDH₂, —CD₂H, or —CD₃,    -   R₁₄ and R₁₅ may each independently be:    -   a methyl group, an ethyl group, an n-propyl group, an iso-propyl        group, an n-butyl group, a sec-butyl group, an iso-butyl group,        a tert-butyl group, an n-pentyl group, a tert-pentyl group, a        neo-pentyl group, an iso-pentyl group, a sec-pentyl group, a        3-pentyl group, a sec-isopentyl group, an n-hexyl group, an        iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an        n-heptyl group, an iso-heptyl group, a sec-heptyl group, a        tert-heptyl group, an n-octyl group, an iso-octyl group, a        sec-octyl group, a tert-octyl group, an n-nonyl group, an        iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an        n-decyl group, an iso-decyl group, a sec-decyl group, a        tert-decyl group, a cyclopentyl group, a cyclohexyl group, a        cycloheptyl group, a cycloctyl group, an adamantanyl group, a        norbornanyl group, a norbornenyl group, a cyclopentenyl group, a        cyclohexenyl group, a cycloheptenyl group, a        bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a        bicyclo[2.2.1]heptyl group, or a bicyclo[2.2.2]octyl group; or    -   a methyl group, an ethyl group, an n-propyl group, an iso-propyl        group, an n-butyl group, a sec-butyl group, an iso-butyl group,        a tert-butyl group, an n-pentyl group, a tert-pentyl group, a        neo-pentyl group, an iso-pentyl group, a sec-pentyl group, a        3-pentyl group, a sec-isopentyl group, an n-hexyl group, an        iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an        n-heptyl group, an iso-heptyl group, a sec-heptyl group, a        tert-heptyl group, an n-octyl group, an iso-octyl group, a        sec-octyl group, a tert-octyl group, an n-nonyl group, an        iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an        n-decyl group, an iso-decyl group, a sec-decyl group, a        tert-decyl group, a cyclopentyl group, a cyclohexyl group, a        cycloheptyl group, a cycloctyl group, an adamantanyl group, a        norbornanyl group, a norbornenyl group, a cyclopentenyl group, a        cyclohexenyl group, a cycloheptenyl group, a        bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a        bicyclo[2.2.1]heptyl group, or a bicyclo[2.2.2]octyl group, each        substituted with at least one deuterium.

In one or more embodiments, in Formula 2, R₁₄ and R₁₅ may eachindependently be selected from —CH₃, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H,—CFH₂, groups represented by Formulae 9-1 to 9-33, groups represented byFormulae 9-1 to 9-33 in which at least one hydrogen is substituted withdeuterium, groups represented by Formulae 10-1 to 10-10, and groupsrepresented by Formulae 10-1 to 10-10 in which at least one hydrogen issubstituted with deuterium, but embodiments of the present disclosureare not limited thereto.

In one or more embodiments, a case where all of R₁₃ to R₁₅ in Formula 2are the same may be excluded.

In one or more embodiments, a case where all of R₁₃ to R₁₅ in Formula 2are each independently a methyl group may be excluded.

At least one selected from R₁₀ and R₁₂ in Formula 1 may eachindependently be a group represented by Formula 3:

In Formula 3, R₁₇ to R₁₉ may each independently be selected from:

-   -   hydrogen, deuterium, a C₁-C₂₀ alkyl group, a C₃-C₁₀ cycloalkyl        group, a C₆-C₆₀ aryl group, and a C₁-C₆₀ heteroaryl group; and    -   a C₁-C₂₀ alkyl group, a C₃-C₁₀ cycloalkyl group, a C₆-C₆₀ aryl        group, and a C₁-C₆₀ heteroaryl group, each substituted with at        least one selected from deuterium and a C₁-C₂₀ alkyl group, and    -   * indicates a binding site to a neighboring atom.

For example, R₁₇ to R₁₉ in Formula 3 may each independently be hydrogenor deuterium.

In an embodiment, one or more selected from R₁₇ to R₁₉ in Formula 3 maybe neither hydrogen nor deuterium. That is, Formula 3 may have two orless benzylic protons.

In one or more embodiments, two or more selected from R₁₇ to R₁₉ inFormula 3 may each independently be neither hydrogen nor deuterium. Thatis, Formula 3 may have one or no benzylic proton.

In an embodiment, in Formula 3,

-   -   R₁₇ to R₁₉ may each independently be hydrogen or deuterium;    -   R₁₇ to R₁₉ may each independently be a methyl group or a        deuterium-containing methyl group;    -   R₁₇ and R₁₈ may each independently be hydrogen or deuterium, and        R₁₈ may be a methyl group or a deuterium-containing methyl        group;    -   R₁₇ may be a methyl group or deuterium-containing methyl group,        and R₁₈ and R₁₉ may each independently be a C₂-C₂₀ alkyl group        or a deuterium-containing C₂-C₂₀ alkyl group;    -   R₁₇ and R₁₈ may each independently be hydrogen or deuterium, and        R₁₈ may be a C₂-C₂₀ alkyl group or a deuterium-containing C₂-C₂₀        alkyl group; or    -   R₁₇ and R₁₈ may each independently be a methyl group or a        deuterium-containing methyl group, and R₁₈ may be a C₂-C₂₀ alkyl        group or a deuterium-containing C₂-C₂₀ alkyl group.

“The C₂-C₂₀ alkyl group or the deuterium-containing C₂-C₂₀ alkyl group”may be selected from:

-   -   an ethyl group, an n-propyl group, an iso-propyl group, an        n-butyl group, a sec-butyl group, an iso-butyl group, a        tert-butyl group, an n-pentyl group, a tert-pentyl group, a        neo-pentyl group, an iso-pentyl group, a sec-pentyl group, a        3-pentyl group, a sec-isopentyl group, an n-hexyl group, an        iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an        n-heptyl group, an iso-heptyl group, a sec-heptyl group, a        tert-heptyl group, an n-octyl group, an iso-octyl group, a        sec-octyl group, a tert-octyl group, an n-nonyl group, an        iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an        n-decyl group, an iso-decyl    -   group, a sec-decyl group, and a tert-decyl group; and an ethyl        group, an n-propyl group, an iso-propyl group, an n-butyl group,        a sec-butyl group, an iso-butyl group, a tert-butyl group, an        n-pentyl group, a tert-pentyl group, a neo-pentyl group, an        iso-pentyl group, a sec-pentyl group, a 3-pentyl group, a        sec-isopentyl group, an n-hexyl group, an iso-hexyl group, a        sec-hexyl group, a tert-hexyl group, an n-heptyl group, an        iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an        n-octyl group, an iso-octyl group, a sec-octyl group, a        tert-octyl group, an n-nonyl group, an iso-nonyl group, a        sec-nonyl group, a tert-nonyl group, an n-decyl group, an        iso-decyl group, a sec-decyl group, and a tert-decyl group, each        substituted with at least one deuterium,    -   but embodiments of the present disclosure are not limited        thereto.

In one or more embodiments, R₁₀ and R₁₂ in Formula 1 may be identical toeach other.

In one or more embodiments, R₁₀ and R₁₂ in Formula 1 may be differentfrom each other.

For example, in Formula 1, R₁₀ may be an ethyl group, and R₁₂ may be amethyl group, an n-propyl group, or an iso-propyl group, but embodimentsof the present disclosure are not limited thereto.

In one or more embodiments, at least one of R₁₀, R₁₂ and R₁₄ in Formulae1 and 2 may each independently be a C₃-C₁₀ cycloalkyl group, or adeuterium-containing C₃-C₁₀ cycloalkyl group.

In Formula 1, at least two selected from R₁ to R₉ and R₁₆ may optionallybe linked to form a C₅-C₃₀ carbocyclic group unsubstituted orsubstituted with at least one R_(1a) or a C₂-C₃₀ heterocyclic groupunsubstituted or substituted with at least one R_(1a).

For example, in Formula 1, at least two selected from R₁ to R₉ and R₁₆may optionally be linked to form a pentadiene group, a cyclohexanegroup, a cycloheptane group, an adamantane group, a bicycle-heptanegroup, a bicycle-octane group, a benzene group, a pyridine group, apyrimidine group, a pyrazine group, a pyridazine group, a naphthalenegroup, an anthracene group, a tetracene group, a phenanthrene group, adihydronaphthalene group, a phenalene group, a benzofuran group, abenzothiophene group, a benzoselenophene group, an indole group, anindene group, a benzosilole group, an azabenzofuran group, anazabenzothiophene group, an azabenzoselenophene group, an azaindolegroup, an azaindene group, and an azabenzosilole group, eachunsubstituted or substituted with at least one R_(1a), but embodimentsof the present disclosure are not limited thereto.

R_(1a) may be the same as defined in connection with R₇.

In one or more embodiments, the organometallic compound represented byFormula 1 may satisfy at least one of Condition 1 to Condition 6:

Condition 1

At least one of R₁ to R₃, R₅ and R₆ in Formula 1 may not be hydrogen.

Condition 2

At least one of R₇ and R₉ in Formula 1 may each independently be a grouphaving two or more carbons.

Condition 3

At least one of R₇ and R₉ in Formula 1 may each independently be asubstituted or unsubstituted C₂-C₆₀ alkyl group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, or a substituted or unsubstitutedC₆-C₆₀ aryl group.

Condition 4

At least one of R₁₀ and R₁₂ in Formula 1 may each independently be agroup represented by Formula 3 and R₁₇ and R₁₉ in Formula 3 may not behydrogen.

Condition 5

At least one of R₁₀ and R₁₂ in Formula 1 may each independently be agroup represented by Formula 3 and at least one of R₁₇ and R₁₉ inFormula 3 may each independently be a C₂-C₂₀ alkyl group, a C₃-C₁₀cycloalkyl group or a C₆-C₆₀ aryl group; or a C₂-C₂₀ alkyl group, aC₃-C₁₀ cycloalkyl group or a C₆-C₆₀ aryl group, each substituted with atleast one selected from deuterium and a C₁-C₂₀ alkyl group.

Condition 6

At least one of R₁₀ and R₁₂ in Formula 1 may each independently be asubstituted or unsubstituted C₃-C₁₀ cycloalkyl group.

In one or more embodiments, when R₄ in Formula 1 is a group representedby Formula 2, R₁₃ in Formula 2 is hydrogen, R₁₄ in Formula 2 is a methylgroup and R₁₅ in Formula 2 is a ethyl group, the organometallic compoundrepresented by Formula 1 may satisfy at least one of Condition 1 toCondition 6.

In one or more embodiments, the organometallic compound may be oneselected from Compounds 1 to 20, but embodiments of the presentdisclosure are not limited thereto:

Formula 1 has the same structure as described herein, but at least oneselected from R₁ to R₆ may each independently be selected from a grouprepresented by Formula 2:

The number of carbon atoms included in Formula 2 may be 4 or more, R₁₃may be hydrogen, deuterium, a C₁-C₂₀ alkyl group, deuterium-containingC₁-C₂₀ alkyl group, a C₃-C₁₀ cycloalkyl group, or a deuterium-containingC₃-C₁₀ cycloalkyl group, R₁₄ and R₁₅ may each independently be a C₁-C₂₀alkyl group, a deuterium-containing C₁-C₂₀ alkyl group, a C₃-C₁₀cycloalkyl group, or a deuterium-containing C₃-C₁₀ cycloalkyl group,and * indicates a binding site to a neighboring atom.

That is, the group represented by Formula 2 may be an alkyl groupincluding one or no benzylic proton, or a derivative of the alkyl group.

Although not particularly limited to any particular theory, a benzylicproton is more chemically reactive than a proton rather than a benzylicproton, and accordingly, a side reaction may be caused by production ofvarious forms of intermediates. However, at least one selected from R₁to R₆ in Formula 1 may each independently be a group represented byFormula 2 which is an alkyl group including one or no benzylic proton,or a derivative of the alkyl group Formula 2. That is, theorganometallic compound represented by Formula 1 may have a stablechemical structure with minimal side reactions occurring before/afterthe synthesis, and at the same time, an electronic device (for example,an organic light-emitting device) including the organometallic compoundrepresented by Formula 1 may have minimal intermolecular interaction ofthe organometallic compound represented by Formula 1 during theoperation. Therefore, an electronic device, for example, an organiclight-emitting device, including the organometallic compound representedby Formula 1 may have improved driving voltage, improved currentdensity, improved external quantum luminescence efficiency, improvedroll off ratio, and improved lifespan.

Synthesis methods of the organometallic compound represented by Formula1 may be recognizable by one of ordinary skill in the art by referringto Synthesis Examples provided below.

The organometallic compound represented by Formula 1 is suitable for usein an organic layer of an organic light-emitting device, for example,for use as a dopant in an emission layer of the organic layer. Thus,another aspect provides an organic light-emitting device that includes:a first electrode; a second electrode; and an organic layer that isdisposed between the first electrode and the second electrode andincludes an organic layer including an emission layer and at least oneorganometallic compound represented by Formula 1.

The organic light-emitting device may have, due to the inclusion of anorganic layer including the organometallic compound represented byFormula 1, improved driving voltage, improved current density, improvedexternal quantum luminescence efficiency, improved roll off ratio, andimproved lifespan.

The organometallic compound of Formula 1 may be used between a pair ofelectrodes of an organic light-emitting device. For example, theorganometallic compound represented by Formula 1 may be included in theemission layer. In this regard, the organometallic compound may act as adopant, and the emission layer may further include a host (that is, inthe emission layer, an amount of the organometallic compound representedby Formula 1 is smaller than an amount of the host).

In an embodiment, the emission layer may emit red light.

The expression “(an organic layer) includes at least one oforganometallic compounds” as used herein may include an embodiment inwhich “(an organic layer) includes identical organometallic compoundsrepresented by Formula 1” and an embodiment in which “(an organic layer)includes two or more different organometallic compounds represented byFormula 1.”

For example, the organic layer may include, as the organometalliccompound, only Compound 1. In this embodiment, Compound 1 may beincluded in an emission layer of the organic light-emitting device. Inone or more embodiments, the organic layer may include, as theorganometallic compound, Compound 1 and Compound 2. In this embodiment,Compound 1 and Compound 2 may be included in an identical layer (forexample, Compound 1 and Compound 2 may both be included in an emissionlayer).

The first electrode may be an anode, which is a hole injectionelectrode, and the second electrode may be a cathode, which is anelectron injection electrode, or the first electrode may be a cathode,which is an electron injection electrode, and the second electrode maybe an anode, which is a hole injection electrode.

In an embodiment, in the organic light-emitting device, the firstelectrode is an anode, and the second electrode is a cathode, and theorganic layer further includes a hole transport region disposed betweenthe first electrode and the emission layer and an electron transportregion disposed between the emission layer and the second electrode,wherein the hole transport region includes a hole injection layer, ahole transport layer, an electron blocking layer, a buffer layer, or anycombination thereof, and wherein the electron transport region includesa hole blocking layer, an electron transport layer, an electroninjection layer, or any combination thereof.

The term “organic layer” as used herein refers to a single layer and/ora plurality of layers disposed between the first electrode and thesecond electrode of the organic light-emitting device. The “organiclayer” may include, in addition to an organic compound, anorganometallic complex including metal.

The FIGURE is a schematic view of an organic light-emitting device 10according to an embodiment. Hereinafter, the structure of an organiclight-emitting device according to an embodiment and a method ofmanufacturing an organic light-emitting device according to anembodiment will be described in connection with the FIGURE. The organiclight-emitting device 10 includes a first electrode 11, an organic layer15, and a second electrode 19, which are sequentially stacked.

A substrate may be additionally disposed under the first electrode 11 orabove the second electrode 19. For use as the substrate, any substratethat is used in general organic light-emitting devices may be used, andthe substrate may be a glass substrate or a transparent plasticsubstrate, each having excellent mechanical strength, thermal stability,transparency, surface smoothness, ease of handling, and waterresistance.

The first electrode 11 may be formed by depositing or sputtering amaterial for forming the first electrode 11 on the substrate. The firstelectrode 11 may be an anode. The material for forming the firstelectrode 11 may be selected from materials with a high work function tofacilitate hole injection. The first electrode 11 may be a reflectiveelectrode, a semi-transmissive electrode, or a transmissive electrode.The material for forming the first electrode may be, for example, indiumtin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO₂), and zincoxide (ZnO). In one or more embodiments, magnesium (Mg), aluminum (Al),aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), ormagnesium-silver (Mg—Ag) may be used as the material for forming thefirst electrode.

The first electrode 11 may have a single-layered structure or amulti-layered structure including two or more layers. For example, thefirst electrode 11 may have a three-layered structure of ITO/Ag/ITO, butthe structure of the first electrode 110 is not limited thereto.

The organic layer 15 is disposed on the first electrode 11.

The organic layer 15 may include a hole transport region, an emissionlayer, and an electron transport region.

The hole transport region may be disposed between the first electrode 11and the emission layer.

The hole transport region may include a hole injection layer, a holetransport layer, an electron blocking layer, a buffer layer, or anycombination thereof.

The hole transport region may include only either a hole injection layeror a hole transport layer. In one or more embodiments, the holetransport region may have a hole injection layer/hole transport layerstructure or a hole injection layer/hole transport layer/electronblocking layer structure, which are sequentially stacked in this statedorder from the first electrode 11.

A hole injection layer may be formed on the first electrode 11 by usingone or more suitable methods selected from vacuum deposition, spincoating, casting, or Langmuir-Blodgett (LB) deposition.

When a hole injection layer is formed by vacuum deposition, thedeposition conditions may vary according to a compound that is used toform the hole injection layer, and the structure and thermalcharacteristics of the hole injection layer. For example, the depositionconditions may include a deposition temperature of about 100° C. toabout 500° C., a vacuum pressure of about 10⁻⁸ torr to about 10⁻³ torr,and a deposition rate of about 0.01 Angstroms per second (Å/sec) toabout 100 Å/sec. However, the deposition conditions are not limitedthereto.

When the hole injection layer is formed using spin coating, coatingconditions may vary according to the material used to form the holeinjection layer, and the structure and thermal properties of the holeinjection layer. For example, a coating speed may be from about 2,000revolutions per minute (rpm) to about 5,000 rpm, and a temperature atwhich a heat treatment is performed to remove a solvent after coatingmay be from about 80° C. to about 200° C. However, the coatingconditions are not limited thereto.

Conditions for forming a hole transport layer and an electron blockinglayer may be understood by referring to conditions for forming the holeinjection layer.

The hole transport region may include at least one selected fromm-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB,methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine(TCTA), polyaniline/dodecylbenzene sulfonic acid (PANI/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrene sulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound represented by Formula 201 below, anda compound represented by Formula 202 below:

In Ar₁₀₁ and Ar₁₀₂ in Formula 201 may each independently be selectedfrom:

-   -   a phenylene group, a pentalenylene group, an indenylene group, a        naphthylene group, an azulenylene group, a heptalenylene group,        an acenaphthylene group, a fluorenylene group, a phenalenylene        group, a phenanthrenylene group, an anthracenylene group, a        fluoranthenylene group, a triphenylenylene group, a pyrenylene        group, a chrysenylenylene group, a naphthacenylene group, a        picenylene group, a perylenylene group, and a pentacenylene        group; and    -   a phenylene group, a pentalenylene group, an indenylene group, a        naphthylene group, an azulenylene group, a heptalenylene group,        an acenaphthylene group, a fluorenylene group, a phenalenylene        group, a phenanthrenylene group, an anthracenylene group, a        fluoranthenylene group, a triphenylenylene group, a pyrenylene        group, a chrysenylenylene group, a naphthacenylene group, a        picenylene group, a perylenylene group, and a pentacenylene        group, each substituted with at least one selected from        deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a        nitro group, an amino group, an amidino group, a hydrazine        group, a hydrazone group, a carboxylic acid group or a salt        thereof, a sulfonic acid group or a salt thereof, a phosphoric        acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀        alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a        C₃-C₁₀ cycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀        heterocycloalkyl group, a C₁-C₁₀ heterocycloalkenyl group, a        C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio        group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromatic        condensed polycyclic group, and a monovalent non-aromatic        condensed heteropolycyclic group.

In Formula 201, xa and xb may each independently be an integer from 0 to5, or may be 0, 1, or 2. For example, xa is 1 and xb is 0, but xa and xbare not limited thereto.

R₁₀₁ to R₁₀₈, R₁₁₁ to R₁₁₉, and R₁₂₁ to R₁₂₄ in Formulae 201 and 202 mayeach independently be selected from:

-   -   hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano        group, a nitro group, an amino group, an amidino group, a        hydrazine group, a hydrazone group, a carboxylic acid group or a        salt thereof, a sulfonic acid group or a salt thereof, a        phosphoric acid group or a salt thereof, a C₁-C₁₀ alkyl group        (for example, a methyl group, an ethyl group, a propyl group, a        butyl group, a pentyl group, a hexyl group, and so on), or a        C₁-C₁₀ alkoxy group (for example, a methoxy group, an ethoxy        group, a propoxy group, a butoxy group, a pentoxy group, and so        on);    -   a C₁-C₁₀ alkyl group or a C₁-C₁₀ alkoxy group, each substituted        with at least one selected from deuterium, —F, —Cl, —Br, —I, a        hydroxyl group, a cyano group, a nitro group, an amino group, an        amidino group, a hydrazine group, a hydrazone group, a        carboxylic acid group or a salt thereof, a sulfonic acid group        or a salt thereof, and a phosphoric acid group or a salt        thereof;    -   a phenyl group, a naphthyl group, an anthracenyl group, a        fluorenyl group, and a pyrenyl group; and    -   a phenyl group, a naphthyl group, an anthracenyl group, a        fluorenyl group, and a pyrenyl group, each substituted with at        least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl        group, a cyano group, a nitro group, an amino group, an amidino        group, a hydrazine group, a hydrazone group, a carboxylic acid        group or a salt thereof, a sulfonic acid group or a salt        thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀        alkyl group, and a C₁-C₁₀ alkoxy group,    -   but embodiments of the present disclosure are not limited        thereto.

R₁₀₉ in Formula 201 may be selected from:

-   -   a phenyl group, a naphthyl group, an anthracenyl group, and a        pyridinyl group; and    -   a phenyl group, a naphthyl group, an anthracenyl group, and a        pyridinyl group, each substituted with at least one selected        from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano        group, a nitro group, an amino group, an amidino group, a        hydrazine group, a hydrazone group, a carboxylic acid group or a        salt thereof, a sulfonic acid group or a salt thereof, a        phosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a        C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, an        anthracenyl group, and a pyridinyl group.

In an embodiment, the compound represented by Formula 201 may berepresented by Formula 201A, but embodiments of the present disclosureare not limited thereto:

R_(101, R111), R₁₁₂, and R₁₀₉ in Formula 201A are the same as describedabove.

For example, the compound represented by Formula 201, and the compoundrepresented by Formula 202 may include compounds HT1 to HT20 illustratedbelow, but are not limited thereto:

A thickness of the hole transport region may be in a range of about 100Angstroms (Å) to about 10,000 Å, for example, about 100 Å to about 1,000Å. When the hole transport region includes at least one of a holeinjection layer and a hole transport layer, the thickness of the holeinjection layer may be in a range of about 100 Å to about 10,000 Å, andfor example, about 100 Å to about 1,000 Å, and the thickness of the holetransport layer may be in a range of about 50 Å to about 2,000 Å, andfor example, about 100 Å to about 1,500 Å. While not wishing to be boundby theory, it is understood that when the thicknesses of the holetransport region, the hole injection layer, and the hole transport layerare within these ranges, satisfactory hole transporting characteristicsmay be obtained without a substantial increase in driving voltage.

The hole transport region may further include, in addition to thesematerials, a charge-generation material for the improvement ofconductive properties. The charge-generation material may behomogeneously or non-homogeneously dispersed in the hole transportregion.

The charge-generation material may be, for example, a p-dopant. Thep-dopant may be one selected from a quinone derivative, a metal oxide,and a cyano group-containing compound, but embodiments of the presentdisclosure are not limited thereto. Non-limiting examples of thep-dopant are a quinone derivative, such as tetracyanoquinonedimethane(TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane(F4-TCNQ); a metal oxide, such as a tungsten oxide or a molybdenumoxide; and a cyano group-containing compound, such as Compound HT-D1below, but are not limited thereto:

The hole transport region may include a buffer layer.

Also, the buffer layer may compensate for an optical resonance distanceaccording to a wavelength of light emitted from the emission layer, andthus, efficiency of a formed organic light-emitting device may beimproved.

Then, an emission layer may be formed on the hole transport region byvacuum deposition, spin coating, casting, LB deposition, or the like.When the emission layer is formed by vacuum deposition or spin coating,the deposition or coating conditions may be similar to those applied informing the hole injection layer although the deposition or coatingconditions may vary according to a compound that is used to form theemission layer.

Meanwhile, when the hole transport region includes an electron blockinglayer, a material for the electron blocking layer may be selected frommaterials for the hole transport region described above and materialsfor a host to be explained later. However, the material for the electronblocking layer is not limited thereto. For example, when the holetransport region includes an electron blocking layer, a material for theelectron blocking layer may be mCP, which will be explained later.

The emission layer may include a host and a dopant, and the dopant mayinclude the organometallic compound represented by Formula 1.

The host may include at least one selected from TPBi, TBADN, ADN (alsoreferred to as “DNA”), CBP, CDBP, TCP, mCP, Compound H50, and CompoundH51:

In one or more embodiments, the host may further include a compoundrepresented by Formula 301:

Ar₁₁₁ and Ar₁₁₂ in Formula 301 may each independently be selected from:

-   -   a phenylene group, a naphthylene group, a phenanthrenylene        group, and a pyrenylene group; and    -   a phenylene group, a naphthylene group, a phenanthrenylene        group, and a pyrenylene group, each substituted with at least        one selected from a phenyl group, a naphthyl group, and an        anthracenyl group.

Ar₁₁₃ to Ar₁₁₂ in Formula 301 may each independently be selected from:

-   -   a C₁-C₁₀ alkyl group, a phenyl group, a naphthyl group, a        phenanthrenyl group, and a pyrenyl group; and    -   a phenyl group, a naphthyl group, a phenanthrenyl group, and a        pyrenyl group, each substituted with at least one selected from        a phenyl group, a naphthyl group, and an anthracenyl group.

g, h, i, and j in Formula 301 may each independently be an integer from0 to 4, and may be, for example, 0, 1, or 2.

Ar₁₁₃ to Ar₁₁₆ in Formula 301 may each independently be selected from:

-   -   a C₁-C₁₀ alkyl group, the substituted with at least one selected        from a phenyl group, a naphthyl group, and an anthracenyl group;    -   a phenyl group, a naphthyl group, an anthracenyl group, a        pyrenyl group, a phenanthrenyl group, and a fluorenyl group;    -   a phenyl group, a naphthyl group, an anthracenyl group, a        pyrenyl group, a phenanthrenyl group, and a fluorenyl group,        each substituted with at least one selected from deuterium, —F,        —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an        amino group, an amidino group, a hydrazine group, a hydrazone        group, a carboxylic acid group or a salt thereof, a sulfonic        acid group or a salt thereof, a phosphoric acid group or a salt        thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀        alkynyl group, a C₁-C₆₀ alkoxy group, a phenyl group, a naphthyl        group, an anthracenyl group, a pyrenyl group, a phenanthrenyl        group, and a fluorenyl group; and

-   -   but embodiments of the present disclosure are not limited        thereto.

In one or more embodiments, the host may include a compound representedby Formula 302 below:

Ar₁₂₂ to Ar₁₂₅ in Formula 302 may each independently the same as definedin connection with Ar₁₁₃ in Formula 301.

Ar₁₂₆ and Ar₁₂₇ in Formula 302 may each independently be a C₁-C₁₀ alkylgroup (for example, a methyl group, an ethyl group, or a propyl group).

k and l in Formula 302 may each independently be an integer from 0 to 4.For example, k and l may be 0, 1, or 2.

When the organic light-emitting device is a full-color organiclight-emitting device, the emission layer may be patterned into a redemission layer, a green emission layer, and a blue emission layer. Inone or more embodiments, due to a stacked structure including a redemission layer, a green emission layer, and/or a blue emission layer,the emission layer may emit white light.

When the emission layer includes a host and a dopant, an amount of thedopant may be in a range of about 0.01 parts to about 15 parts by weightbased on 100 parts by weight of the host, but embodiments of the presentdisclosure are not limited thereto.

A thickness of the emission layer may be in a range of about 100 Å toabout 1,000 Å, for example, about 200 Å to about 600 Å. While notwishing to be bound by theory, it is understood that when the thicknessof the emission layer is within this range, excellent light-emissioncharacteristics may be obtained without a substantial increase indriving voltage.

Then, an electron transport region may be disposed on the emissionlayer.

The electron transport region may include a hole blocking layer, anelectron transport layer, an electron injection layer, or anycombination thereof.

For example, the electron transport region may have a hole blockinglayer/electron transport layer/electron injection layer structure or anelectron transport layer/electron injection layer structure, but thestructure of the electron transport region is not limited thereto. Theelectron transport layer may have a single-layered structure or amulti-layered structure including two or more different materials.

Conditions for forming the hole blocking layer, the electron transportlayer, and the electron injection layer which constitute the electrontransport region may be understood by referring to the conditions forforming the hole injection layer.

When the electron transport region includes a hole blocking layer, thehole blocking layer may include, for example, at least one of BCP,BPhen, and BAlq but embodiments of the present disclosure are notlimited thereto:

A thickness of the hole blocking layer may be in a range of about 20 Åto about 1,000 Å, for example, about 30 Å to about 300 Å. While notwishing to be bound by theory, it is understood that when the thicknessof the hole blocking layer is within these ranges, the hole blockinglayer may have improved hole blocking ability without a substantialincrease in driving voltage.

The electron transport layer may further include at least one selectedfrom BCP, BPhen, Alq₃, BAlq, TAZ, and NTAZ:

In one or more embodiments, the electron transport layer may include atleast one of ET1 to ET25, but are not limited thereto:

A thickness of the electron transport layer may be in a range of about100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. Whilenot wishing to be bound by theory, it is understood that when thethickness of the electron transport layer is within the range describedabove, the electron transport layer may have satisfactory electrontransport characteristics without a substantial increase in drivingvoltage.

Also, the electron transport layer may further include, in addition tothe materials described above, a metal-containing material.

The metal-containing material may include a Li complex. The Li complexmay include, for example, Compound ET-D1 (lithium 8-hydroxylquinolate,LiQ) or ET-D2:

The electron transport region may include an electron injection layerthat promotes flow of electrons from the second electrode 19 thereinto.

The electron injection layer may include at least one selected from LiF,NaCl, CsF, Li₂O, and BaO.

A thickness of the electron injection layer may be in a range of about 1Å to about 100 Å, for example, about 3 Å to about 90 Å. While notwishing to be bound by theory, it is understood that when the thicknessof the electron injection layer is within the range described above, theelectron injection layer may have satisfactory electron injectioncharacteristics without a substantial increase in driving voltage.

The second electrode 19 is disposed on the organic layer 15. The secondelectrode 19 may be a cathode. A material for forming the secondelectrode 19 may be selected from metal, an alloy, an electricallyconductive compound, and a combination thereof, which have a relativelylow work function. For example, lithium (Li), magnesium (Mg), aluminum(Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In),or magnesium-silver (Mg—Ag) may be used as a material for forming thesecond electrode 19. In one or more embodiments, to manufacture atop-emission type light-emitting device, a transmissive electrode formedusing ITO or IZO may be used as the second electrode 19.

Hereinbefore, the organic light-emitting device has been described withreference to the FIGURE, but embodiments of the present disclosure arenot limited thereto.

Another aspect of the present disclosure provides a diagnosticcomposition including at least one organometallic compound representedby Formula 1.

The organometallic compound represented by Formula 1 provides highluminescent efficiency. Accordingly, a diagnostic composition includingthe organometallic compound may have high diagnostic efficiency.

The diagnostic composition may be used in various applications includinga diagnosis kit, a diagnosis reagent, a biosensor, and a biomarker.

The term “C₁-C₆₀ alkyl group” as used herein refers to a linear orbranched saturated aliphatic hydrocarbon monovalent group having 1 to 60carbon atoms, and non-limiting examples thereof include a methyl group,an ethyl group, a propyl group, an iso-butyl group, a sec-butyl group, atert-butyl group, a pentyl group, an iso-amyl group, and a hexyl group.The term “C₁-C₆₀ alkylene group” as used herein refers to a divalentgroup having the same structure as the C₁-C₆₀ alkyl group.

The term “C₁-C₆₀ alkoxy group” as used herein refers to a monovalentgroup represented by —OA₁₀₁ (wherein A₁₀₁ is the C₁-C₆₀ alkyl group),and non-limiting examples thereof include a methoxy group, an ethoxygroup, and an iso-propyloxy group.

The term “C₂-C₆₀ alkenyl group” as used herein refers to a hydrocarbongroup formed by including at least one double bond in the middle or atthe terminus of the C₂-C₆₀ alkyl group, and examples thereof include anethenyl group, a propenyl group, and a butenyl group. The term “C₂-C₆₀alkenylene group” as used herein refers to a divalent group having thesame structure as the C₂-C₆₀ alkenyl group.

The term “C₂-C₆₀ alkynyl group” as used herein refers to a hydrocarbongroup formed by including at least one triple bond in the middle or atthe terminus of the C₂-C₆₀ alkyl group, and examples thereof include anethynyl group, and a propynyl group. The term “C₂-C₆₀ alkynylene group”as used herein refers to a divalent group having the same structure asthe C₂-C₆₀ alkynyl group.

The term “C₃-C₁₀ cycloalkyl group” as used herein refers to a monovalentsaturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, andnon-limiting examples thereof include a cyclopropyl group, a cyclobutylgroup, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.The term “C₃-C₁₀ cycloalkylene group” as used herein refers to adivalent group having the same structure as the C₃-C₁₀ cycloalkyl group.

The term “C₁-C₁₀ heterocycloalkyl group” as used herein refers to amonovalent saturated monocyclic group having at least one heteroatomselected from N, O, P, Si and S as a ring-forming atom and 1 to 10carbon atoms, and non-limiting examples thereof include atetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term“C₁-C₁₀ heterocycloalkylene group” as used herein refers to a divalentgroup having the same structure as the C₁-C₁₀ heterocycloalkyl group.

The term “C₃-C₁₀ cycloalkenyl group” as used herein refers to amonovalent monocyclic group that has 3 to 10 carbon atoms and at leastone double bond in the ring thereof and no aromaticity, and non-limitingexamples thereof include a cyclopentenyl group, a cyclohexenyl group,and a cycloheptenyl group. The term “C₃-C₁₀ cycloalkenylene group” asused herein refers to a divalent group having the same structure as theC₃-C₁₀ cycloalkenyl group.

The term “C₁-C₁₀ heterocycloalkenyl group” as used herein refers to amonovalent monocyclic group that has at least one heteroatom selectedfrom N, O, P, Si, and S as a ring-forming atom, 1 to 10 carbon atoms,and at least one double bond in its ring. Examples of the C₁-C₁₀heterocycloalkenyl group are a 2,3-dihydrofuranyl group, and a2,3-dihydrothiophenyl group. The term “C₁-C₁₀ heterocycloalkenylenegroup” as used herein refers to a divalent group having the samestructure as the C₁-C₁₀ heterocycloalkenyl group.

The term “C₆-C₆₀ aryl group” as used herein refers to a monovalent grouphaving a carbocyclic aromatic system having 6 to 60 carbon atoms, andthe term “C₆-C₆₀ arylene group” as used herein refers to a divalentgroup having a carbocyclic aromatic system having 6 to 60 carbon atoms.Non-limiting examples of the C₆-C₆₀ aryl group include a phenyl group, anaphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenylgroup, and a chrysenyl group. When the C₆-C₆₀ aryl group and the C₆-C₆₀arylene group each include two or more rings, the rings may be fused toeach other.

The term “C₁-C₆₀ heteroaryl group” as used herein refers to a monovalentgroup having a heterocyclic aromatic system that has at least oneheteroatom selected from N, O, P, Si, and S as a ring-forming atom, and1 to 60 carbon atoms. The term “C₁-C₆₀ heteroarylene group” as usedherein refers to a divalent group having a heterocyclic aromatic systemthat has at least one heteroatom selected from N, O, P, Si, and S as aring-forming atom, and 1 to 60 carbon atoms. Non-limiting examples ofthe C₁-C₆₀ heteroaryl group include a pyridinyl group, a pyrimidinylgroup, a pyrazinyl group, a pyridazinyl group, a triazinyl group, aquinolinyl group, and an isoquinolinyl group. When the C₁-C₆₀ heteroarylgroup and the C₁-C₆₀ heteroarylene group each include two or more rings,the rings may be fused to each other.

The term “C₆-C₆₀ aryloxy group” as used herein indicates —OA₁₀₂ (whereinA₁₀₂ is the C₆-C₆₀ aryl group), and a C₆-C₆₀ arylthio group as usedherein indicates —SA₁₀₃ (wherein A₁₀₃ is the C₆-C₆₀ aryl group).

The term “monovalent non-aromatic condensed polycyclic group” as usedherein refers to a monovalent group (for example, having 8 to 60 carbonatoms) having two or more rings condensed to each other, only carbonatoms as ring-forming atoms, and no aromaticity in its entire molecularstructure. Examples of the monovalent non-aromatic condensed polycyclicgroup include a fluorenyl group. The term “divalent non-aromaticcondensed polycyclic group” as used herein refers to a divalent grouphaving the same structure as the monovalent non-aromatic condensedpolycyclic group.

The term “monovalent non-aromatic condensed heteropolycyclic group” asused herein refers to a monovalent group (for example, having 2 to 60carbon atoms) having two or more rings condensed to each other, aheteroatom selected from N, O, P, Si, and S, other than carbon atoms, asa ring-forming atom, and no aromaticity in its entire molecularstructure. Non-limiting examples of the monovalent non-aromaticcondensed heteropolycyclic group include a carbazolyl group. The term“divalent non-aromatic condensed heteropolycyclic group” as used hereinrefers to a divalent group having the same structure as the monovalentnon-aromatic condensed heteropolycyclic group.

The term “C₅-C₃₀ carbocyclic group” as used herein refers to a saturatedor unsaturated cyclic group having, as a ring-forming atom, 5 to 30carbon atoms only. The C₅-C₃₀ carbocyclic group may be a monocyclicgroup or a polycyclic group.

The term “C₂-C₃₀ heterocyclic group” as used herein refers to asaturated or unsaturated cyclic group having, as a ring-forming atom, atleast one heteroatom selected from N, O, Si, P, and S other than 2 to 30carbon atoms. The C₂-C₃₀ heterocyclic group may be a monocyclic group ora polycyclic group.

At least one substituent selected from substituted C₅-C₃₀ carbocyclicgroup, the substituted C₂-C₃₀ heterocyclic group, the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀ alkenyl group, the substitutedC₂-C₆₀ alkynyl group, the substituted C₁-C₆₀ alkoxy group, thesubstituted C₃-C₁₀ cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenyl group, thesubstituted C₁-C₁₀ heterocycloalkenyl group, the substituted C₆-C₆₀ arylgroup, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀ heteroaryl group, the substitutedmonovalent non-aromatic condensed polycyclic group, and the substitutedmonovalent non-aromatic condensed heteropolycyclic group may be selectedfrom:

-   -   deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H,        —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino        group, an amidino group, a hydrazine group, a hydrazone group, a        carboxylic acid group or a salt thereof, a sulfonic acid group        or a salt thereof, a phosphoric acid group or a salt thereof, a        C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl        group, and a C₁-C₆₀ alkoxy group;    -   a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl        group, and a C₁-C₆₀ alkoxy group, each substituted with at least        one selected from deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H,        —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a        nitro group, an amino group, an amidino group, a hydrazine        group, a hydrazone group, a carboxylic acid group or a salt        thereof, a sulfonic acid group or a salt thereof, a phosphoric        acid group or a salt thereof, a C₃-C₁₀ cycloalkyl group, a        C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a        C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀        aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl        group, a monovalent non-aromatic condensed polycyclic group, a        monovalent non-aromatic condensed heteropolycyclic group,        —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), —Ge(Q₁₃)(Q₁₄)(Q₁₅),        —B(Q₁₆)(Q₁₇), —P(═O)(Q₁₈)(Q₁₉), and —P(Q₁₈)(Q₁₉);    -   a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a        C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a        C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio        group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromatic        condensed polycyclic group, and a monovalent non-aromatic        condensed heteropolycyclic group;    -   a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a        C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a        C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio        group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromatic        condensed polycyclic group, and a monovalent non-aromatic        condensed heteropolycyclic group, each substituted with at least        one selected from deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H,        —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a        nitro group, an amino group, an amidino group, a hydrazine        group, a hydrazone group, a carboxylic acid group or a salt        thereof, a sulfonic acid group or a salt thereof, a phosphoric        acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀        alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a        C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a        C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a        C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio        group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromatic        condensed polycyclic group, a monovalent non-aromatic condensed        heteropolycyclic group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅),        —Ge(Q₂₃)(Q₂₄)(Q₂₅), —B(Q₂₆)(Q₂₇), —P(═O)(Q₂₈)(Q₂₉), and        —P(Q₂₈)(Q₂₉); and    -   —N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), —Ge(Q₃₃)(Q₃₄)(Q₃₅),        —B(Q₃₆)(Q₃₇), —P(═O)(Q₃₈)(Q₃₉), and —P(Q₃₈)(Q₃₉), and    -   Q₁ to Q₉, Q₁₁ to Q₁₉, Q₂₁ to Q₂₉, and Q₃₁ to Q₃₉ may each        independently be selected from hydrogen, deuterium, —F, —Cl,        —Br, —I, a hydroxyl group, a cyano group, a nitro group, an        amino group, an amidino group, a hydrazine group, a hydrazone        group, a carboxylic acid group or a salt thereof, a sulfonic        acid group or a salt thereof, a phosphoric acid group or a salt        thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀        alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group,        a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a        C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀        aryl group substituted with at least one selected from a C₁-C₆₀        alkyl group, and a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a        C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalent        non-aromatic condensed polycyclic group, and a monovalent        non-aromatic condensed heteropolycyclic group.

Hereinafter, a compound and an organic light-emitting device accordingto embodiments are described in detail with reference to SynthesisExample and Examples. However, the organic light-emitting device is notlimited thereto. The wording “B was used instead of A” as used indescribing Synthesis Examples means that an amount of A used wasidentical to an amount of B used, in terms of a molar equivalent.

EXAMPLES Synthesis Example 1 (Compound 2)

Synthesis of Intermediate 2(1)

1-chloro-6-(sec-butyl)isoquinoline (4.56 grams (g), 20.76 millimoles,mmol), (3,5-dimethylphenyl)boronic acid (4.67 g, 31.14 mmol), Pd(PPh₃)₄(1.92 g, 1.66 mmol), and K₂CO₃ (7.17 g, 51.90 mmol) were mixed with 60milliliters (mL) of tetrahydrofuran (THF) and 30 mL of distilled water,and the mixed solution was stirred under reflux for 18 hours. After thetemperature was cooled to room temperature, methylene chloride (MC) wasused to extract the organic layer, and then, anhydrous magnesium sulfate(MgSO₄) was added to dry the organic layer. The resulting solution wasfiltered, and the filtrate was evaporated to produce a residue. Theresidue was then purified by column chromatography with EA:Hexane=1:10as an eluent, thereby producing Intermediate 2(1) (5.60 g, yield of93%).

MALDI-TOFMS (m/z): C₂₁H₂₃N (M+) 289.

Synthesis of Intermediate 2(2)

Intermediate 2(1) (5.58 g, 19.3 mmol) and iridium chloride hydrate (3.02g) were mixed with 45 mL of ethoxyethanol and 15 mL of distilled water,and the mixed solution was stirred under reflux for 24 hours. After areaction was complete, the temperature was cooled to room temperature.The resulting solids produced form the reaction were separated byfiltration and thoroughly washed with water/methanol/hexane sequentiallyto produce a solid product. The solid product was dried in a vacuumoven, thereby producing Intermediate 2(2) (3.9 g, yield of 50.3%).

Synthesis of Compound 2

Intermediate 2(2) (1.30 g, 0.81 mmol),2,2,6,6-tetramethylheptane-3,5-dione (1.49 g, 8.14 mmol), and Na₂CO₃(0.83 g, 8.14 mmol) were mixed with 15 mL of ethoxyethanol, and themixed solution was stirred under reflux for 24 hours. After a reactionwas complete, the resulting solids produced form the reaction wereseparated by filtration and thoroughly washed using ethanol and hexaneto produce residues. The residues were purified by column chromatographywith dichloromethane:n-hexane=1:1 (v/v) as an eluent, thereby producingCompound 2 (0.78 g, yield of 50.6%). Then, Compound 2 was identified byMass and HPLC.

HRMS(MALDI) calcd for C₅₃H₆₃IrN₂O₂: m/z 952.4519. Found: 952.4517.

Synthesis Example 2 (Compound 4)

Compound 4 (0.96 g, yield of 58.5%) was synthesized in the same manneras in Synthesis Example 1, except that3,7-diethyl-3,7-dimethylnonane-4,6-dione was used instead of2,2,6,6-tetramethylheptane-3,5-dione in the production of Compound 2.

HRMS(MALDI) calcd for C₅₇H₇₁IrN₂O₂: m/z 1008.5145. Found: 1008.5149

Synthesis Example 3 (Compound 1)

Synthesis of Intermediate 1(1)

Intermediate 1(1) was synthesized in the same manner as in the synthesisof Intermediate 2(1) of Synthesis Example 1, except that7-sec-butyl-1-chloroisoquinoline was used instead of1-chloro-6-(sec-butyl)isoquinoline.

Synthesis of Intermediate 1(2)

Intermediate 1(2) was synthesized in the same manner as in the synthesisof Intermediate 2(2) of Synthesis Example 1, except that Intermediate1(1) was used instead of Intermediate 2(1).

Synthesis of Compound 1

Compound 1 (0.99 g, yield of 70.8%) was synthesized in the same manneras in the synthesis of Compound 2 of Synthesis Example 1, except thatIntermediate 1(2) and pentane-2,4-dione were used instead ofIntermediate 2(2) and 2,2,6,6-tetramethylheptane-3,5-dione,respectively.

HRMS(MALDI) calcd for C₄₇H₅₁IrN₂O₂: m/z 868.3580. Found: 868.3588

Synthesis Example 4 (Compound 17)

Synthesis of Intermediate 17(1)

Intermediate 17(1) (5.85 g, yield of 85%) of was synthesized in the samemanner as in the synthesis of Intermediate 2(1) of Synthesis Example 1,except that (3-t-butyl-5-methylphenyl)boronic acid was used instead of(3,5-dimethylphenyl)boronic acid.

HRMS(MALDI) calcd for C₂₄H₂₉N: m/z 331.2300. Found: 331.2311.

Synthesis of Intermediate 17(2)

Intermediate 17(2) was synthesized in the same manner as in thesynthesis of Intermediate 2(2) of Synthesis Example 1, except thatIntermediate 17(1) was used instead of Intermediate 2(1).

Synthesis of Compound 17

Compound 17 (1.06 g, yield of 63.2%) was synthesized in the same manneras in the synthesis of Compound 2 of Synthesis Example 1, except thatIntermediate 17(1) was used instead of Intermediate 2(2).

HRMS(MALDI) calcd for C₅₉H₇₅IrN₂O₂: m/z 1036.5458. Found: 1036.5464.

Synthesis Example 5 (Compound 18)

Synthesis of Intermediate 18(1)

Intermediate 18(1) (5.95 g, yield of 87%) was synthesized in the samemanner as in the synthesis of Intermediate 2(1) of Synthesis Example 1,except that 1-chloro-6-(cyclopentyl)Isoquinoline (5.39 g, 20.76 mmol)was used instead of 1-chloro-6-(sec-butyl)isoquinoline.

HRMS(MALDI) calcd for C₂₄H₂₉N: m/z 331.2300. Found: 331.2311.

Synthesis of Intermediate 18(2)

Intermediate 18(2) was synthesized in the same manner as in thesynthesis of Intermediate 2(2) of Synthesis Example 1, except thatIntermediate 18(1) was used instead of Intermediate 2(1).

Synthesis of Compound 18

Compound 18 (0.68 g, yield of 41%) was synthesized in the same manner asin the synthesis of Compound 2 of Synthesis Example 1, except thatIntermediate 18(2) was used instead of Intermediate 2(2).

HRMS(MALDI) calcd for C₅₉H₇₁IrN₂O₂: m/z 1032.5145. Found: 1032.5151.

Synthesis Example 6 (Compound 20)

Compound 20 (0.96 g, yield of 59.2%) was synthesized in the same manneras in the synthesis of Compound 2 of Synthesis Example 1, except that1,3-dicyclohexylpropane-1,3-dione was used instead of2,2,6,6-tetramethylheptane-3,5-dione.

HRMS(MALDI) calcd for C₅₇H₆₇IrN₂O₂: m/z 1004.4832. Found: 1004.4841

Example 1

As an anode, a glass substrate, on which ITO/Ag/ITO (70 Å/1,000 Å/70)was deposited, was cut to a size of 50 mm×50 mm×0.5 mm (mm=millimeter),sonicated with iso-propyl alcohol and pure water each for 5 minutes, andcleaned by exposure to ultraviolet rays and ozone for 30 minutes. Then,the glass substrate was provided to a vacuum deposition apparatus.

2-TNATA was vacuum-deposited on the anode of the glass substrate to forma hole injection layer having a thickness of 600 Å, and4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) wasvacuum-deposited on the hole injection layer to form a hole transportlayer having a thickness of 1,350 Å.

Next, CBP (host) and Compound 1 (dopant) were co-deposited on the holetransport layer at a weight ratio of 98:2 to form an emission layerhaving a thickness of 400 Å.

Afterwards, BCP was vacuum-deposited on the emission layer to form ahole blocking layer having a thickness of 50 Å, Alq₃ wasvacuum-deposited on the hole blocking layer to form an electrontransport layer having a thickness of 350 Å, LiF was deposited on theelectron transport layer to form an electron injection layer having athickness of 10 Å, and Mg and Ag were co-deposited on the electroninjection layer at a weight ratio of 90:10 to form a cathode having athickness of 120 Å, thereby completing an organic light-emitting device(emitting red light):

Examples 2 to 6 and Comparative Examples A to F

Organic light-emitting devices were manufactured in the same manner asin Example 1, except that in forming an emission layer, for use as adopant, corresponding compounds shown in Table 1 were used instead ofCompound 1.

Evaluation Example 1: Evaluation on Characteristics of OrganicLight-Emitting Devices

The driving voltage, current density, external quantum luminescentefficiency (EQE), roll-off ratio, full width at half maximum (FWHM) andpeak wavelength of emission peaks in EL spectra, and lifespan (LT₉₇) ofthe organic light-emitting devices manufactured according to Examples 1to 6 and Comparative Examples A to F were evaluated, and results thereofare shown in Table 1. Here, devices used in the evaluation are acurrent-voltage meter (Keithley 2400) and a luminance meter (MinoltaCs-1000A), and the lifespan (T₉₇) (at 3,500 nit) indicates an amount oftime that elapsed when luminance was 97% of initial luminance (100%).The roll-off ratio was calculated by Equation 20:Roll off ratio={1−(efficiency(at 3,500 nit)/maximum luminanceefficiency)}×100%  Equation 20

TABLE 1 Roll- Dopant in Driving Current Max Off peak emission voltagedensity EQE ratio FWHM wavelength LT₉₇ layer (V) (mA/cm²) (%) (%) (nm)(nm) (hr) Example 1 Compound 1 5.52 23.7 24.2 17 61.9 629 320 Example 2Compound 2 5.40 17.5 28.6 12 54.64 626 460 Example 3 Compound 4 5.0316.2 29.3 13 48.62 624 450 Example 4 Compound 17 5.12 16.8 28.6 12 52.12622 370 Example 5 Compound 18 5.40 17.2 28.9 12 53.35 626 370 Example 6Compound 20 5.34 19.3 27.5 13 54.56 625 310 Comparative Compound A 5.4912.2 20.4 28 82.39 623 50 Example A Comparative Compound B 9.82 670.213.7 89 23.6 652 1 Example B Comparative Compound C 5.80 20.0 25.9 1359.41 616 150 Example C Comparative Compound D 6.01 23.5 21.7 16 67.51630 42 Example D Comparative Compound E 5.48 22.3 22.8 16 62.24 629 48Example E Comparative Compound F 5.40 22.7 23.4 14 59.94 629 28 ExampleF

In Compound A, n-Hex indicates an n-hexyl group.

Referring to Table 1, it was confirmed that the organic light-emittingdevices of Examples 1 to 6 showed improved driving voltage, improvedcurrent density, improved external quantum luminescent efficiency,improved roll-off ratio, and improved lifespan characteristics comparedto those of the organic light-emitting device of Comparative Examples Ato F.

According to the one or more embodiments, an organometallic compound hasexcellent electric characteristics and thermal stability, and thus, anorganic light-emitting device including the organometallic compoundshows excellent driving voltage, emission efficiency, quantum emissionefficiency, roll-off ratio, and lifespan characteristics.

It should be understood that embodiments described herein should beconsidered in a descriptive sense only and not for purposes oflimitation. Descriptions of features or aspects within each embodimentshould typically be considered as available for other similar featuresor aspects in other embodiments.

While one or more embodiments have been described with reference to thefigures, it will be understood by those of ordinary skill in the artthat various changes in form and details may be made therein withoutdeparting from the spirit and scope as defined by the following claims.

What is claimed is:
 1. An organometallic compound represented by Formula1:

wherein, in Formula 1, R₁ to R₃, R₆ to R₁₂ and R₁₆ are eachindependently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a substituted or unsubstitutedC₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group,a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅),—Ge(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), —P(═O)(Q₈)(Q₉), and —P(Q₈)(Q₉), R₄ isselected from a group represented by Formula 2,

wherein, the number of carbon atoms included in Formula 2 is 4 or more,R₁₃ in Formula 2 is hydrogen, deuterium, a C₁-C₂₀ alkyl group, adeuterium-containing C₁-C₂₀ alkyl group, a C₃-C₁₀ cycloalkyl group, or adeuterium-containing C₃-C₁₀cycloalkyl group, R₁₄ in Formula 2 is aC₁-C₂₀ alkyl group, deuterium-containing C₁-C₂₀ alkyl group, a C₃-C₁₀cycloalkyl group, or a deuterium-containing C₃-C₁₀ cycloalkyl group, R₁₅in Formula 2 is a C₂-C₂₀ alkyl group, deuterium-containing C₂-C₂₀ alkylgroup, a C₃-C₁₀ cycloalkyl group, or a deuterium-containing C₃-C₁₀cycloalkyl group, * indicates a binding site to a neighboring atom,provided that, i) at least one selected from R₁, R₂, R₃, R₅, R₆, R₇, R₈,R₉, R₁₀, R₁₁, R₁₂, R₁₃, R₁₄, R₁₅ and R₁₆ in Formulae 1 and 2 is eachindependently a C₃-C₁₀ cycloalkyl group or a deuterium-containing C₃-C₁₀cycloalkyl group, or ii) R₁₀ in Formula 1 is independently a grouprepresented by Formula 3:

wherein, in Formula 3, R₁₇ to R₁₉ are each independently selected from:a C₁-C₂₀ alkyl group, a C₃-C₁₀ cycloalkyl group, a C₆-C₆₀ aryl group,and a C₁-C₆₀ heteroaryl group; and a C₁-C₂₀ alkyl group, a C₃-C₁₀cycloalkyl group, a C₆-C₆₀ aryl group, and a C₁-C₆₀ heteroaryl group,each substituted with at least one selected from deuterium and a C₁-C₂₀alkyl group, and * indicates a binding site to a neighboring atom, atleast one substituent of the substituted C₁-C₆₀ alkyl group, thesubstituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group,the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkylgroup, the substituted C₁-C₁₀ heterocycloalkyl group, the substitutedC₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀ heterocycloalkenylgroup, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxygroup, the substituted C₆-C₆₀ arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted monovalent non-aromatic condensedpolycyclic group, and the substituted monovalent non-aromatic condensedheteropolycyclic group is selected from: deuterium, —F, —Cl, —Br, —I,—CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group; a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group,a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group, each substituted withat least one selected from deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H,—CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —N(Q₁₁)(Q₁₂),—Si(Q₁₃)(Q₁₄)(Q₁₅), —Ge(Q₁₃)(Q₁₄)(Q₁₅), —B(Q₁₆)(Q₁₇), —P(═O)(Q₁₈)(Q₁₉),and —P(Q₁₈)(Q₁₉); a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, and a monovalent non-aromatic condensed heteropolycyclic group; aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,—CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅),—Ge(Q₂₃)(Q₂₄)(Q₂₅), —B(Q₂₆)(Q₂₇), —P(═O)(Q₂₈)(Q₂₉), and —P(Q₂₈)(Q₂₉);and —N(Q₃1)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), —Ge(Q₃₃)(Q₃₄)(Q₃₅), —B(Q₃₆)(Q₃₇),—P(═O)(Q₃₈)(Q₃₉), and —P(Q₃₈)(Q₃₉), and Q₁ to Q₉, Q₁₁ to Q₁₉, Q₂₁ toQ₂₉, and Q₃₁ to Q₃₉ are each independently selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryl group substituted with at least oneselected from a C₁-C₆₀ alkyl group, and a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, and a monovalentnon-aromatic condensed heteropolycyclic group.
 2. The organometalliccompound of claim 1, wherein R₁ to R₃, R₅ to R₁₂ and R₁₆ are eachindependently selected from: hydrogen, deuterium, a methyl group, anethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, asec-butyl group, an iso-butyl group, a tert-butyl group, an n-pentylgroup, a tert-pentyl group, a neopentyl group, an iso-pentyl group, asec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexylgroup, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, ann-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptylgroup, an n-octyl group, an iso-octyl group, a sec-octyl group, atert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonylgroup, a tert-nonyl group, an n-decyl group, an iso-decyl group, asec-decyl group, a tert-decyl group, a methoxy group, an ethoxy group, apropoxy group, a butoxy group, a pentoxy group, a cyclopentyl group, acyclohexyl group, a cycloheptyl group, a cycloctyl group, an adamantanylgroup, a norbornanyl group, a norbornenyl group, a cyclopentenyl group,a cyclohexenyl group, a cycloheptenyl group, bicyclo[1.1.1]pentyl,bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, a bicyclo[2.2.2]octyl group,a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, apyridinyl group, a pyrimidinyl group, a carbazolyl group, a fluorenylgroup, a dibenzosilolyl group, a dibenzofuranyl group, adibenzothiophenyl group, or —Si(Q₃)(Q₄)(Q₅); a methyl group, an ethylgroup, an n-propyl group, an iso-propyl group, an n-butyl group, asec-butyl group, an iso-butyl group, a tert-butyl group, an n-pentylgroup, a tert-pentyl group, a neopentyl group, an iso-pentyl group, asec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexylgroup, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, ann-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptylgroup, an n-octyl group, an iso-octyl group, a sec-octyl group, atert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonylgroup, a tert-nonyl group, an n-decyl group, an iso-decyl group, asec-decyl group, and a tert-decyl group, each substituted with at leastone deuterium; and a methoxy group, an ethoxy group, a propoxy group, abutoxy group, a pentoxy group, a cyclopentyl group, a cyclohexyl group,a cycloheptyl group, a cycloctyl group, an adamantanyl group, anorbornanyl group, a norbomenyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, bicyclo[1.1.1]pentyl,bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, a bicyclo[2.2.2]octyl group,a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, apyridinyl group, a pyrimidinyl group, a carbazolyl group, a fluorenylgroup, a dibenzosilolyl group, a dibenzofuranyl group, and adibenzothiophenyl group, each substituted with at least one selectedfrom deuterium and a C₁-C₁₀ alkyl group, and Q₃ to Q₅ are eachindependently selected from: —CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃,—CH₂CD₂H, —CH₂CDH₂, —CHDCH₃, —CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃,—CD₂CD₂H, and —CD₂CDH₂; an n-propyl group, an iso-propyl group, ann-butyl group, an iso-butyl group, a sec-butyl group, a tert-butylgroup, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, atert-pentyl group, a phenyl group, and a naphthyl group; and an n-propylgroup, an iso-propyl group, an n-butyl group, an iso-butyl group, asec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentylgroup, a sec-pentyl group, a tert-pentyl group, a phenyl group, and anaphthyl group, each substituted with at least one selected fromdeuterium, a C₁-C₁₀ alkyl group, and a phenyl group.
 3. Theorganometallic compound of claim 1, wherein, in Formula 1, R₇ and R₉ arenot hydrogen, and R₇ and R₉ are identical to each other.
 4. Theorganometallic compound of claim 1, wherein, in Formula 1, R₇ and R₉ arenot hydrogen, and R₇ and R₉ are different from each other.
 5. Theorganometallic compound of claim 1, wherein R₁₃ in Formula 2 is hydrogenor deuterium.
 6. The organometallic compound of claim 1, wherein R₁₃ inFormula 2 is a C₁-C₂₀ alkyl group, a deuterium-containing C₁-C₂₀ alkylgroup, a C₃-C₁₀ cycloalkyl group, or a deuterium-containing C₃-C₁₀cycloalkyl group.
 7. The organometallic compound of claim 1, wherein R₁₄and R₁₅ in Formula 2 are different from each other.
 8. Theorganometallic compound of claim 1, wherein, in Formula 2, R₁₃ ishydrogen, deuterium, —CH₃, —CDH₂, —CD₂H, or —CD₃, R₁₄ is: a methylgroup, an ethyl group, an n-propyl group, an iso-propyl group, ann-butyl group, a sec-butyl group, an iso-butyl group, a tert-butylgroup, an n-pentyl group, a tert-pentyl group, a neopentyl, aniso-pentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentylgroup, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, atert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptylgroup, a tert-heptyl group, an n-octyl group, an iso-octyl group, asec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonylgroup, a sec-nonyl group, a tert-nonyl group, an n-decyl group, aniso-decyl group, a sec-decyl group, a tert-decyl group, a cyclopentylgroup, a cyclohexyl group, a cycloheptyl group, a cycloctyl group, anadamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group,bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, or abicyclo[2.2.2]octyl group; or a methyl group, an ethyl group, ann-propyl group, an iso-propyl group, an n-butyl group, a sec-butylgroup, an iso-butyl group, a tert-butyl group, an n-pentyl group, atert-pentyl group, a neopentyl, an iso-pentyl group, a sec-pentyl group,a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an iso-hexylgroup, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, aniso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octylgroup, an iso-octyl group, a sec-octyl group, a tert-octyl group, ann-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonylgroup, an n-decyl group, an iso-decyl group, a sec-decyl group, atert-decyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cycloctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl,bicyclo[2.2.1]heptyl, or a bicyclo[2.2.2]octyl group, each substitutedwith at least one deuterium, and R₁₅ is: an ethyl group, an n-propylgroup, an iso-propyl group, an n-butyl group, a sec-butyl group, aniso-butyl group, a tert-butyl group, an n-pentyl group, a tert-pentylgroup, a neopentyl, an iso-pentyl group, a sec-pentyl group, a 3-pentylgroup, a sec-isopentyl group, an n-hexyl group, an iso-hexyl group, asec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptylgroup, a sec-heptyl group, a tert-heptyl group, an n-octyl group, aniso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonylgroup, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, ann-decyl group, an iso-decyl group, a sec-decyl group, a tert-decylgroup, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acycloctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl,bicyclo[2.2.1]heptyl, or a bicyclo[2.2.2]octyl group; or an ethyl group,an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butylgroup, an iso-butyl group, a tert-butyl group, an n-pentyl group, atert-pentyl group, a neopentyl, an iso-pentyl group, a sec-pentyl group,a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an iso-hexylgroup, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, aniso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octylgroup, an iso-octyl group, a sec-octyl group, a tert-octyl group, ann-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonylgroup, an n-decyl group, an iso-decyl group, a sec-decyl group, atert-decyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cycloctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl,bicyclo[2.2.1]heptyl, or a bicyclo[2.2.2]octyl group, each substitutedwith at least one deuterium.
 9. The organometallic compound of claim 1,wherein each of at least one selected from R₁₀ and R₁₂ in Formula 1 isindependently a group represented by Formula 3:

wherein, in Formula 3, R₁₇ to R₁₉ are each independently selected from:hydrogen, deuterium, a C₁-C₂₀ alkyl group, a C₃-C₁₀ cycloalkyl group, aC₆-C₆₀ aryl group, and a C₁-C₆₀ heteroaryl group; and a C₁-C₂₀ alkylgroup, a C₃-C₁₀ cycloalkyl group, a C₆-C₆₀ aryl group, and a C₁-C₆₀heteroaryl group, each substituted with at least one selected fromdeuterium and a C₁-C₂₀ alkyl group, and * indicates a binding site to aneighboring atom.
 10. The organometallic compound of claim 1, whereinR₁₀ and R₁₂ in Formula 1 are identical to each other.
 11. Theorganometallic compound of claim 1, wherein R₁₀ and R₁₂ in Formula 1 aredifferent from each other.
 12. The organometallic compound of claim 1,wherein at least one selected from R₇, R₁₀, R₁₂, and R₁₄ in Formulae 1and 2 is each independently a C₃-C₁₀ cycloalkyl group or adeuterium-containing C₃-C₁₀ cycloalkyl group.
 13. The organometalliccompound of claim 1, wherein the organometallic compound is one ofCompounds 2, 4, 10, 11, and 13 to 20:


14. An organic light-emitting device comprising: a first electrode;second electrode; and an organic layer disposed between the firstelectrode and the second electrode, wherein the organic layer comprisesan emission layer and at least one organometallic compound of claim 1.15. The organic light-emitting device of claim 14, wherein the firstelectrode is an anode, the second electrode is a cathode, the organiclayer further comprises a hole transport region disposed between thefirst electrode and the emission layer and an electron transport regiondisposed between the second electrode and the emission layer, whereinthe hole transport region comprises a hole injection layer, a holetransport layer, an electron blocking layer, a buffer layer, or anycombination thereof, and wherein the electron transport region comprisesa hole blocking layer, an electron transport layer, an electroninjection layer, or any combination thereof.
 16. The organiclight-emitting device of claim 14, wherein the emission layer comprisesthe organometallic compound.
 17. The organic light-emitting device ofclaim 16, wherein the emission layer emits red light.
 18. The organiclight-emitting device of claim 16, wherein the emission layer furthercomprises a host, and an amount of the host is greater than that of theorganometallic compound in the emission layer.
 19. A diagnosticcomposition comprising at least one organometallic compound of claim 1.